Non-1,2-epoxy Or Nonphenolic Reactant Contains One Or More Nitrogen Atoms Patents (Class 528/119)
  • Patent number: 5204385
    Abstract: A curing agent for a water borne epoxy resin composition wherein the curing agent is the reaction product of a chemical excess of a polyfunctional epoxide compound and a quaternary ammonium salt in which substantially all of the excess epoxide groups in the reaction product are subsequently consumed in a reaction with a polyamine. A process for preparing the curing agent and a hardenable film forming coating composition containing as essential components, the curing agent, at least one water dispersible epoxy resin and water is also disclosed.
    Type: Grant
    Filed: November 27, 1990
    Date of Patent: April 20, 1993
    Assignee: Reichhold Chemicals, Inc.
    Inventor: Bryan A. Naderhoff
  • Patent number: 5093471
    Abstract: Novel mesogenic amine curing agent for reactive monomers, such as epoxy resins and diisocyanates, comprises a mesogenic moiety, a primary amine, and a flexible alkyl spacer connected between the mesogenic moiety and the primary amine and wherein the alkyl spacer is a saturated, linear alkyl group having from about one to about twenty carbon atoms. Novel mesogenic amine has the formula: ##STR1## where M is --O--, ##STR2## or --CH.sub.2 --, where R is --NO.sub.2 or --CN, andwhere x is 1 to 20.Novel mesogenic amine has a labile group subject to cross-linking and the formula: ##STR3## where K is ##STR4## where L is ##STR5## where M is --o--, ##STR6## or --CH.sub.2 --, where Z is cinnamate, an alkene having from one to ten carbons, an isocyanate, an alkoxy, or an alcohol having from one to ten carbons,where T is a cyano, a nitro or an alkyl group having from about one to ten carbons, andwhere X is 1 to 20.
    Type: Grant
    Filed: December 7, 1989
    Date of Patent: March 3, 1992
    Assignee: Kent State University
    Inventor: John L. West
  • Patent number: 5089547
    Abstract: A cross-linked low surface adhesion composition, that can be utilized as either an electrographic toner powder or as an additive for conventional electrographic toner powder, exhibits improved transfer and contributes to an increase in the useful life of the developer. The low surface adhesion composition employs a silicone resin and a polyester resin cross-linked with a polyfunctional epoxy novolac resin.
    Type: Grant
    Filed: August 6, 1990
    Date of Patent: February 18, 1992
    Assignee: Eastman Kodak Company
    Inventors: John M. McCabe, John C. Wilson
  • Patent number: 5057559
    Abstract: Cationic paint binders based on the reaction products of epoxide compounds with substituted carbamic acid derivatives and the use thereof in the formulation of cathodically deposited paints are described. The carbamic acid derivatives are urethanes, ureas, allophanates, and biuret compounds. Crosslinking functionality and/or protonatable groups are introduced by a suitable selection of blocking agents for the isocyanate compounds utilized. The reaction between the epoxide compounds and carbamic acid derivatives takes place in the presence of basic groups under relatively mild conditions; and, even when several carbamic acid moieties are present in a molecule, a readily soluble product is obtained.
    Type: Grant
    Filed: September 6, 1988
    Date of Patent: October 15, 1991
    Assignee: Vianova Kunstharz, A.G.
    Inventors: Willibald Paar, Rudolf Schipfer
  • Patent number: 5045609
    Abstract: A matrix resin system, for the preparation of composite parts, is comprised of a major amount of cyanate resin and an epoxy resin modified by reaction with an isocyanate. The resin system can be toughened by the addition of thermoplastic material, the toughness improvement being enhanced by the addition of a polyester rubber additive. The modified epoxy resin system is itself a resin having good modulus and Tg characteristics. The resin is cured at temperatures of 250.degree.-400.degree. F. in the presence of a metallic complex catalyst, and OH donor.
    Type: Grant
    Filed: July 7, 1989
    Date of Patent: September 3, 1991
    Assignee: Hexcel Corporation
    Inventors: Frank W. Lee, Kenneth S. Baron, Maureen Boyle
  • Patent number: 5043411
    Abstract: The present invention generally relates to a thermosettable cyanate ester resin composition which contains a fortifier that is the reaction product of an epoxy and an aromatic reactant selected from an aromatic amine and an aromatic amide. Thermoset cyanate ester resin compositions of the present invention have improved flexural strength and/or flexural modulus. The compositions of the present invention may be used to prepare circuit boards or molded parts.
    Type: Grant
    Filed: May 14, 1990
    Date of Patent: August 27, 1991
    Assignee: Nova Petrochemicals Inc.
    Inventors: Kam W. Ho, Adrian Cassola
  • Patent number: 5039720
    Abstract: An aqueous electrophoretic coating material, which can be deposited at the cathode and contains(A) 90 to 50% by weight, based on the total portion of synthetic resin vehicle, of one or several polycondensation, polymerization and/or poly-addition resins, the resin or, in the event that several resins are present, their mixture(a) having a number average molecular weight (Mn) of 700 to 10,000(b) having 1.2.times.10.sup.23 to 21.7.times.10.sup.23 lateral or terminal double bonds per 1,000 g, corresponding to a hydrogenation iodine number of 5 to 90,(c) optionally containing primary and/or secondary hydroxyl groups, corresponding to a hydroxyl number of 0 to 450 mg KOH/g of resin, and(d) tertiary amino groups corresponding to an amine number of 30 to 450 mg KOH/g of resin.
    Type: Grant
    Filed: September 30, 1988
    Date of Patent: August 13, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Dietrich Saatweber, Georg Hendriux, Gerhard Brindopke, Helmut Plum
  • Patent number: 5025077
    Abstract: A glue composition comprises a heat-hardenable resin, urea and possibly one or several glue additives, and is characterized by the presence of an additional gluing compound is polyol having a functionality of at least equal to three. This glue can be used for mineral fibers in the manufacture of insulation products having improved properties.
    Type: Grant
    Filed: July 28, 1988
    Date of Patent: June 18, 1991
    Assignee: Isover Saint-Gobain
    Inventors: Serge Tetart, Bernard Lericque
  • Patent number: 5025067
    Abstract: An epoxy resin comprising an active hydrogen compound having at least three active hydrogen atoms capable of reacting with an epoxy group in its molecule or butadine or isoprene as a main monomer is modified with an oligomer having on average at least 1.5 equivalents of active hydrogen capable of reacting with an epoxy group in its molecule. An epoxy resin modified with a bisphenol and a compound having active hydrogen or acid anhydride groups capable of reacting with an epoxy group is also provided. A toner containing the epoxy resin as a binder is useful in electrostatography.
    Type: Grant
    Filed: November 16, 1988
    Date of Patent: June 18, 1991
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Yohzoh Yamamoto, Goro Suzuki, Hideo Nakamura, Kiyomi Yasuda
  • Patent number: 5015673
    Abstract: A synthetic resin which carries basic nitrogen groups and is water-dilutable by protonation with acid is obtainable by reacting(A) an epoxy resin having an average molecular weight M.sub.n of from 300 to 6,000 and on average from 1.5 to 3.0 epoxy groups per molecule with(B) a ketimine of a primary amine additionally containing one or more urethane groups and optionally also with(C) a diketimine of a diprimary amine containing no urethane groups and optionally also with(D) a secondary amine which may contain a tertiary amino group also, a ketimine of a primary monoamine and/or a ketimine of a primary/tertiary diamine.
    Type: Grant
    Filed: May 25, 1990
    Date of Patent: May 14, 1991
    Assignee: BASF Lacke & Farben Aktiengesellschaft
    Inventors: Thomas Perner, Rolf Osterloh, Eberhard Schupp, Thomas Schwerzel, Klaas Ahlers
  • Patent number: 5015672
    Abstract: A synthetic resin which carries basic nitrogen groups and is water-dilutable by protonation with acid is obtainable by reacting(A) an epoxy resin having an average molecular weight M.sub.n of from 300 to 6,000 and on average from 1.5 to 3.0 epoxy groups per molecule with(B) a ketimine of a primary amine additionally containing one or more urethane groups and optionally also with(C) a diketimine of a diprimary amine containing no urethane groups and optionally also with(D) a secondary amine which may contain a tertiary amino group also, a ketimine of a primary monoamine and/or a ketimine of a primary/tertiary diamine.
    Type: Grant
    Filed: May 25, 1990
    Date of Patent: May 14, 1991
    Assignee: BASF Lacke & Farben Aktiengesellschaft
    Inventors: Thomas Perner, Rolf Osterloh, Eberhard Schupp, Thomas Schwerzel, Klaas Ahlers
  • Patent number: 5006412
    Abstract: A reaction product of a .beta.-diketone and a polymer having groups that are reactive with the .beta.-diketone can be complexed with a metal. The reaction product having the complex metal can be activated to provide a substrate suitable for plating from an electroless metal plating bath.
    Type: Grant
    Filed: July 27, 1989
    Date of Patent: April 9, 1991
    Assignee: International Business Machines Corporation
    Inventors: Susan A. Hodgson, Jae M. Park, Richard R. Thomas
  • Patent number: 4996286
    Abstract: A latent curing agent for epoxy resin, characterized in that the latent curing agent is the hydrazides of the formula (I);(NH.sub.2 NHCOCH.sub.2 CH.sub.2).sub.2 N(CH.sub.2).sub.11 CONHNH.sub.2 (I)The present curing agent is useful in formulating storable, one-package, heat-curable epoxy resin-based compositions.
    Type: Grant
    Filed: February 15, 1985
    Date of Patent: February 26, 1991
    Assignee: Ajinomoto Co., Inc.
    Inventors: Kiyomiki Hirai, Koji Takeuchi, Nobuo Ito, Masahiro Abe
  • Patent number: 4959398
    Abstract: A powdery adhesive comprised of spherical particles comprising 40 to 90 parts by weight of an epoxy resin component, 10 to 60 parts by weight of a rubber component and a latent curing agent contained inside the particles, the average particle size of the particles being from 0.1 to 500 .mu.m. The powdery adhesive may be prepared by a process comprising a step of preparing a compatible mixture comprising an epoxy resin component, a rubber component and a common organic solvent, a step of emulsifying or suspending the compatible mixture in an aqueous medium to form spherical particles, and a step of causing a phase separation of the epoxy resin component and the rubber component in the spherical particles.
    Type: Grant
    Filed: February 13, 1989
    Date of Patent: September 25, 1990
    Assignee: Toray Industries, Inc.
    Inventors: Koichiro Oka, Ikuo Hagiwara
  • Patent number: 4956402
    Abstract: A synthetic resin which carries basic nitrogen groups and is water-dilutable by protonation with acid is obtainable by reacting(A) an epoxy resin having an average molecular weight M.sub.n of from 200 to 6,000 and on average from 1.5 to 3.0 epoxy groups per molecule with(B) a ketimine of a primary amine additionally containing one or more urethane groups and optionally also with(C) a diketimine of a diprimary amine containing no urethane groups and optionally also with(D) a secondary amine which may contain a tertiary amimo group also, a ketimine of a primary monoamine and/or a ketimine of a primary/tertiary diamine.
    Type: Grant
    Filed: June 23, 1988
    Date of Patent: September 11, 1990
    Assignee: BASF Lacke & Farben Aktiengesellschaft
    Inventors: Thomas Perner, Rolf Osterloh, Eberhard Schupp, Thomas Schwerzel, Klaas Ahlers
  • Patent number: 4950722
    Abstract: The invention relates to an unsaturated-epoxy moiety R--NHCO.sub.2 --E wherein R is unsaturated and free of isocyanate functionality and E has an oxirane ring. The moiety may be dissolved in a liquid epoxy compound. The invention also relates to a mixture obtained by vinyl polymerization of the moiety and an added unsaturated compound in the liquid epoxy compound solution. Epoxy cross-linking then leads to a polymeric reaction product. Vinyl polymerization and epoxy curing can also be simultaneous. A polymeric material is formed by reacting an isocyanate compound having the formula R--NCO with an epoxy compound having the formula E--OH, where R and E are as defined above, to form the moiety R--NHCO.sub.2 --E and polymerizing this moiety, along with an additional unsaturated compound under vinyl polymerization conditions and in the presence of a liquid epoxy compound, to form a copolymer of R--NHCO.sub.2 --E with the additional unsaturated compound.
    Type: Grant
    Filed: January 5, 1989
    Date of Patent: August 21, 1990
    Assignee: The Dow Chemical Company
    Inventor: Theodore L. Parker
  • Patent number: 4935478
    Abstract: Hot-curable compositions of matter containing (a) an unsaturated imide of the formula I ##STR1## (b) a benzaldehyde derivative of the formula II ##STR2## in which for example M=2, n=zero, o=1 R.sup.1, R.sup.2 and R.sup.3 are each hydrogen and R is 4,4'diphenylmethane are suitable for the production of mouldings having excellent thermostability and resistance to thermal ageing.
    Type: Grant
    Filed: July 29, 1988
    Date of Patent: June 19, 1990
    Assignee: Ciba-Geigy Corporation
    Inventor: Andreas Kramer
  • Patent number: 4931496
    Abstract: Fiber-reinforced compositions comprising a structural fiber and a cyanate ester resin formulation having an N-substituted urea compound as a latent cure accelerator provide rapid-curing prepreg with good out-time characteristics. The prepreg may be used to form composite articles with good toughness and excellent retention of properties on extended exposure to moisture at elevated temperatures.
    Type: Grant
    Filed: March 24, 1989
    Date of Patent: June 5, 1990
    Assignee: Amoco Corporation
    Inventors: Shahid P. Qureshi, Hugh C. Gardner, Richard H. Newman-Evans
  • Patent number: 4929650
    Abstract: A coating material for a tendon for prestressed concrete includes a curing composition, the curing time of which is so controlled that the composition is held in an uncured fluid state for a predetermined time after the concrete hardens. After the predetermined time passes, the composition cures. By coating a tendon for prestressed concrete with the coating material having such properties, an antirust effect of the tendon, an improved adhering force of the tendon to the concrete and a decreased cost of manufacturing prestressed concrete can be obtained.
    Type: Grant
    Filed: July 25, 1988
    Date of Patent: May 29, 1990
    Assignees: Mitsui Sekiyu Kagaku Kogyo Kabushiki Kaisha, Shinko Kosen Kogyo Kabushiki Kaisha
    Inventors: Makoto Kurauchi, Michio Hashimoto, Kiyoshi Hayasaki, Toshikazu Minami, Mutsuhiko Ohnishi, Yohei Suzuki
  • Patent number: 4918157
    Abstract: Urea compounds having a plurality of substituents selected from hydrogen, substituted hydrocarbyl radicals and unsubstituted hydrocarbyl radicals are good latent cure accelerators for thermosetting cyanate resin formulations. The resulting cyanate resin formulations are useful as coatings, adhesives and as impregnating resins, particularly in applications where extended storage at or near room temperature is desired.
    Type: Grant
    Filed: September 28, 1988
    Date of Patent: April 17, 1990
    Assignee: Amoco Corporation
    Inventors: Hugh C. Gardner, Richard H. Newman-Evans
  • Patent number: 4888407
    Abstract: The present invention provides an improved epoxy resin composition comprising an epoxy resin and a novel imide compound represented by the formula ##STR1## wherein X represents an --NH.sub.2 group and/or --OH group, Ar.sub.1 and Ar.sub.2 independently represent an aromatic residue, R.sub.1 represents a hydrogen atom or an alkyl group having from 1 to 10 carbon atoms, R.sub.2 represents a hydrogen atom, an alkyl or alkoxy group having from 1 to 20 carbon atoms or hydroxyl group, and each of m and n represents a number of from 0 to 30.
    Type: Grant
    Filed: December 28, 1987
    Date of Patent: December 19, 1989
    Assignee: Sumitomo Chemical Co., Ltd.
    Inventors: Saito Yasuhisa, Kunimasa Kamio, Mitsuhiro Shibata, Katsuya Watanabe, Yutaka Shiomi, Youichi Ueda
  • Patent number: 4868253
    Abstract: A reaction product of a .beta.-diketone and a polymer having groups that are reactive with the .beta.-diketone can be complexed with a metal. The reaction product having the complex metal can be activated to provide a substrate suitable for plating from an electroless metal plating bath.
    Type: Grant
    Filed: April 19, 1988
    Date of Patent: September 19, 1989
    Assignee: International Business Machines Corporation
    Inventors: Susan A. Hodgson, Jae M. Park, Richard R. Thomas
  • Patent number: 4859788
    Abstract: Amino group containing curing component (A) for compounds (B) which contain epoxy or 1,3-dioxolan-2-one groups, comprising a reaction product of (a.sub.1) active CH alkyl esters of isocyanate adducts thereof with (a.sub.2) polyamines.Mixtures of (A) and (B) with or without diluents and additives give rapid curing even at low temperatures and high atmospheric humidity and are suitable in particular for paint formulations.
    Type: Grant
    Filed: April 7, 1988
    Date of Patent: August 22, 1989
    Assignee: Hoechst AG
    Inventors: Gerhard Brindopke, Claus Godau, Walter Weber
  • Patent number: 4820797
    Abstract: Thermoset products are prepared by polymerizing (A) at least one thermosettable compound which contains both a maleimide group and a cyanate group such as 3-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)phenyl cyanate and optionally (B) at least one of (1) at least one aromatic polycyanate such as bisphenol A dicyanate; (2) at least one polymaleimide such as N,N'-(methylenedi-p-phenylene)bismaleimide; (3) at least one material having an average of more than one vicinal epoxide group per molecule such as a diglycidyl ether of bisphenol A; (4) at least one polymerizable ethylenically unsaturated material such as styrene; or (5) a mixture of any two or more of components 1-4 in any combination.
    Type: Grant
    Filed: May 17, 1988
    Date of Patent: April 11, 1989
    Assignee: The Dow Chemical Company
    Inventor: Robert E. Hefner, Jr.
  • Patent number: 4820798
    Abstract: Thermoset products are prepared by polymerizing (A) at least one thermosettable compound which contains both a maleimide group and a cyanate group such as 3-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)phenyl cyanate and optionally (B) at least one of (1) at least one aromatic polycyanate such as bisphenol A dicyanate; (2) at least one polymaleimide such as N,N'-(methylenedi-p-phenylene)bismaleimide; (3) at least one material having an average of more than one vicinal epoxide group per molecule such as a diglycidyl ether of bisphenol A; (4) at least one polymerizable ethylenically unsaturated material such as styrene; or (5) a mixture of any two or more of components 1-4 in any combination.
    Type: Grant
    Filed: May 17, 1988
    Date of Patent: April 11, 1989
    Assignee: The Dow Chemical Company
    Inventor: Robert E. Hefner, Jr.
  • Patent number: 4806677
    Abstract: Hardeners are described for synthetic resins which contain groups which are capable of ester or amide formation and, if appropriate, polymerizable double bonds. The new hardeners, which allow lower crosslinking temperatures, are products (A) of the Michael addition of compounds (B), containing Michael addition-capable ester groups, to compounds (C) which contain at least two Michael addition-capable double bonds, the products (A) having an average of at least one polymerization-capable double bond and at least two transesterification- or transamidation-capable ester groups per molecule and the compound (B) representing products of the reaction of (b1) CH-active alkyl esters and (b2) polyisocyanates.
    Type: Grant
    Filed: January 29, 1987
    Date of Patent: February 21, 1989
    Assignee: Hoechst AG
    Inventors: Gerd Walz, Helmut Plum
  • Patent number: 4804740
    Abstract: Urea compounds having a plurality of substituents selected from hydrogen, substituted hydrocarbyl radicals and unsubstituted hydrocarbyl radicals are good latent cure accelerators for thermosetting cyanate resin formulations. The resulting cyanate resin formulations are useful as coatings, adhesives and as impregnating resins, particularly in applications where extended storage at or near room temperature is desired.
    Type: Grant
    Filed: July 8, 1987
    Date of Patent: February 14, 1989
    Assignee: Amoco Corporation
    Inventors: Hugh C. Gardner, Richard H. Newman-Evans
  • Patent number: 4795787
    Abstract: Novel curing agents for synthetic resins containing groups capable of ester formation or amide formation and, optionally polymerizable double bonds which are Michael addition products of monocarboxylic or dicarboxylic acid esters, capable of undergoing Michael addition, with compounds containing at least two double bonds capable of undergoing Michael addition, the two components being reacted in such ratios that the Michael addition product contains at least one ester group capable of transesterification and/or transamidation and at least one polymerizable double bond.
    Type: Grant
    Filed: October 5, 1987
    Date of Patent: January 3, 1989
    Assignee: Hoechst AG
    Inventor: Gerd Walz
  • Patent number: 4785075
    Abstract: Polycyanate esters of polyhydric phenols are cured with a liquid solution of a metal acetylacetonate in an alkylphenol. Such cured compositions are useful in structural composites, transfer molded-encapsulants, filmed structural adhesives and printed wiring boards.
    Type: Grant
    Filed: July 27, 1987
    Date of Patent: November 15, 1988
    Assignee: Interez, Inc.
    Inventor: David A. Shimp
  • Patent number: 4774282
    Abstract: Novel curable resin compositions are disclosed containing an aromatic cyanate ester and an allyl ether of a bisphenol as a modifier. These compositions provide improved prepregs and composites. Additional modifiers including epoxy resins and bismaleimides may be included.
    Type: Grant
    Filed: November 20, 1986
    Date of Patent: September 27, 1988
    Assignee: Amoco Corporation
    Inventor: Shahid P. Qureshi
  • Patent number: 4772643
    Abstract: A crosslinked and chain extended urethane-epoxy copolymer coating with high performance properties typical of two part urethane solution coatings results from cure at ambient temperatures (e.g. 70.degree. F.) when the two aqueous systems are merely mixed, stirred and spread at the site. One aqueous system is a dispersion of polyepoxides. The other aqueous system is a primary amine-terminated urethane oligomer in which no less than about 25% and no more than about 40% of the amine functionality is substituted by a salt of a volatile acid which aids dispersion of the oligomer. Minimal organic solvent is present, and as the acid evaporates, the primary amine is restored for linking with the epoxy groups.
    Type: Grant
    Filed: December 11, 1987
    Date of Patent: September 20, 1988
    Assignee: Tennant Company
    Inventors: G. Dale Ernst, Alan R. Schuweiler
  • Patent number: 4764579
    Abstract: An adhesive mixture comprising a multiplicity of contiguous deposits of a curable but uncured fluid resin and a fluid curing agent for the resin, said deposits being separated by a thin flexible barrier film of cured resin resulting from the interaction between the resin and curing agent.
    Type: Grant
    Filed: July 7, 1987
    Date of Patent: August 16, 1988
    Assignee: The Oakland Corporation
    Inventor: Richard B. Wallace
  • Patent number: 4749743
    Abstract: Disclosed herein is a low molecular weight epoxy-functional polyurethane and high solids thermosetting coating compositions prepared therewith.
    Type: Grant
    Filed: October 6, 1986
    Date of Patent: June 7, 1988
    Assignee: PPG Industries, Inc.
    Inventors: Ronald R. Ambrose, Samuel Porter, Jr.
  • Patent number: 4746727
    Abstract: Polymeric compositions are prepared from ethylenically unsaturated monomeric compositions and polyarylcyanate ester compositions which have at least two arylcyanate ester moieties bridged by a polycyclic aliphatic moiety; and wherein the polyarylcyanate ester composition is substantially soluble in the ethylenically unsaturated monomeric composition.
    Type: Grant
    Filed: February 11, 1986
    Date of Patent: May 24, 1988
    Assignee: The Dow Chemical Company
    Inventors: Gary W. Bogan, Peter A. Lucas
  • Patent number: 4742147
    Abstract: Liquid, solventless, complex polymeric compositions are provided which thermoset at ambient temperatures through addition polymerization. In a preferred embodiment, a two component system includes a first component comprising amine or acrylate terminated polyurethanes, polyurethane-ureas or polyureas and a second component comprising di or polyacrylates. By adding an excess of acrylate, a one component system can be formed which thermosets when exposed to ultraviolet radiation.
    Type: Grant
    Filed: October 11, 1985
    Date of Patent: May 3, 1988
    Inventor: Gus Nichols
  • Patent number: 4739028
    Abstract: Epoxy resins have been found to be fortified (increased in strength and modulus yet not made brittle) by compounding:(a) a resin-forming polyepoxide(b) an amine curing agent for (a) and(c) a fortifier for (a)+(b) comprising the reaction product of(i) an aromatic polyhydroxy compound and(ii) a diepoxide with one epoxy group less reactive than the other:and heat curing the mixture. Strengths as high as 140 MPa and moduli as high as 4500 MPa have been attained with a ductile mode of failure.
    Type: Grant
    Filed: March 2, 1987
    Date of Patent: April 19, 1988
    Assignee: Canadian Patents & Development Limited
    Inventors: Paul D. McLean, Andrew Garton, Robert F. Scott
  • Patent number: 4732961
    Abstract: A spherical particulate adhesive comprising particles of a partially amine cured epoxy resin as the main component and having an average particle size of 0.3 to 500 .mu.m, in which particles of the epoxy resin contain an at least partially compatible agent homogeneously in the interior thereof. This adhesive is a heat-curable adhesive and has a very high bonding force. After bonding, the adhesive is chemically stable and is especially preferably used for bonding in the field of electronic material, such as liquid crystal display devices, which are apt to be degraded by impurities and for which high-precision bonding is required.
    Type: Grant
    Filed: September 18, 1986
    Date of Patent: March 22, 1988
    Assignee: Toray Industries, Inc.
    Inventor: Koichiro Oka
  • Patent number: 4728555
    Abstract: Process for the preparation of .beta.-hydroxypolyamines by reaction of polyepoxide compounds with ammonia, in which at least one polyepoxide compound is treated in a first stage with liquid ammonia at temperatures below 50.degree. C., a homogeneous phase being formed, after which the reaction between the polyepoxide compound and ammonia is carried out in a second stage at 60.degree. to 130.degree. C., and when the reaction is complete, the excess ammonia is removed from the reaction mixture.The resulting .beta.-hydroxypolyamines are used as binders or--in protonated form--as binders which can be diluted with water, by themselves or in combination with suitable crosslinking agents.
    Type: Grant
    Filed: August 15, 1986
    Date of Patent: March 1, 1988
    Assignee: Hoechst AG
    Inventors: Hans-Joachim Kiessling, Wilhelm Riemenschneider
  • Patent number: 4721770
    Abstract: N-Cyanocarboxylic acid amide derivatives which contain two or three ##STR1## groupings in the molecule are useful as hardeners for epoxide resins.
    Type: Grant
    Filed: June 24, 1986
    Date of Patent: January 26, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Friedrich Stockinger, Friedrich Lohse, Roland Moser
  • Patent number: 4705842
    Abstract: The present invention provides a process for hardening epoxide resin masses, wherein there is added a solution of dicyandiamide and cyanamide in a weight ratio of from 0 to 10:1 in at least one organic solvent.The present invention also provides a hardener solution for epoxide resin masses, consisting of dicyandiamide and cyanamide in a weight ratio of 0 to 10:1 and at least one organic solvent.
    Type: Grant
    Filed: March 21, 1986
    Date of Patent: November 10, 1987
    Assignee: SKW Trostberg Aktiengesellschaft
    Inventor: Joachim von Seyerl
  • Patent number: 4699933
    Abstract: The present invention is directed to polyurethane compositions containing triazine or both triazine and oxazoline or imino carbamate groups which are prepared by reacting:1.(a) at least one alkoxylated hydroxy aromatic oligomer containing at least one triazine group, or(b) at least one alkoxylated hydroxy aromatic oligomer containing at least one triazine group and at least one oxazoline group, or(c) at least one alkoxylated hydroxy aromatic oligomer containing at least one triazine group and at least one imino carbamate group, or(d) at least one alkoxylated hydroxy aromatic oligomer containing at least one triazine group and at least one other N-heterocyclic group, or(e) a mixture of the above and2. at least one material having more than one isocyanate group per moleculewherein the components are employed in proportions which provide a ratio of isocyanate groups to hydroxy groups of from about 0.05:1.0 to about 10.0:1.0, preferably from about 0.95:1.0 to about 1.5:1.0.
    Type: Grant
    Filed: October 14, 1986
    Date of Patent: October 13, 1987
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Mary N. White
  • Patent number: 4695605
    Abstract: A structural adhesive which is particularly useful in vertical substrates is composed of a mixture of two components, the first component being an epoxy resin component comprising a poly epoxide and a polyisocyanate which has been allowed to react with less than an equivalent weight of a polyamine which is a primary or secondary polyamine and the second component being a hardener for the polyepoxide comprising a mixture of primary, secondary and tertiary amines, amido amines and phenolics.
    Type: Grant
    Filed: October 1, 1986
    Date of Patent: September 22, 1987
    Assignee: Ashland Oil, Inc.
    Inventor: Anil B. Goel
  • Patent number: 4686272
    Abstract: An adhesive mixture comprising a multiplicity of contiguous deposits of a curable but uncured fluid resin and a fluid curing agent for the resin, said deposits being separated by a thin flexible barrier film of cured resin resulting from the interaction between the resin and curing agent.
    Type: Grant
    Filed: July 10, 1985
    Date of Patent: August 11, 1987
    Assignee: The Oakland Corporation
    Inventor: Richard B. Wallace
  • Patent number: 4675374
    Abstract: Solventless polymeric compositions suitable for coatings and moldings are formed by the addition reaction product of a first component comprising mono, di or polyamines, or an adduct of mono, di or polyamines with mono, di or polyfunctional acrylates and/or epoxides and a second component comprising mono, di or polyacrylates or mixtures with mono, di or polyepoxides.
    Type: Grant
    Filed: July 18, 1985
    Date of Patent: June 23, 1987
    Inventor: Gus Nichols
  • Patent number: 4663398
    Abstract: Hydroxyaromatic oligomers are prepared by (I) reacting (A) an aromatic hydroxyl-containing material such as bisphenol A with (B) a cyanogen halide such as cyanogen bromide in the presence of a base such as triethylamine and (II) co-oligomerizing the cyanate-containing product from (I) with (C) a polymaleimide such as the reaction product of maleic anhydride with methylenedianiline optionally in the presence of (D) a co-oligomerization catalyst such as cobalt naphthenate. These oligomers are useful in the preparation of epoxy resins.
    Type: Grant
    Filed: February 24, 1986
    Date of Patent: May 5, 1987
    Assignee: The Dow Chemical Company
    Inventor: Robert E. Hefner, Jr.
  • Patent number: 4656207
    Abstract: Disclosed is a stiff, tough thermoset composite, the composite comprising a crosslinked epoxy resin matrix and high strength filaments. The resin matrix comprises a glassy discontinuous phase dispersed in a glassy continuous phase that continues throughout the resin matrix. Volume fractions of the discontinuous phase are at least about 35% of the total volume of the continuous and discontinuous phases combined in exceptionally tough composites.Also disclosed are novel resin compositions suitable for making these thermosets.
    Type: Grant
    Filed: February 19, 1985
    Date of Patent: April 7, 1987
    Assignee: Hercules Incorporated
    Inventors: Harold Jabloner, Brian J. Swetlin, Sung G. Chu
  • Patent number: 4656208
    Abstract: Described are novel thermosetting epoxy resin compositions suitable for making cured resins, prepregs and stiff, tough thermoset composites. The thermosetting compositions comprise a polyepoxide component, an amine hardener and a specified amount of certain aromatic oligomers containing functional groups which are reactive with the polyepoxide and/or hardener under curing conditions for the composition. The cured resins have a multiphase morphology which comprises at least one glassy continuous phase and at least one glassy discontinuous phase and have a fracture toughness, K.sub.IC, of at least 1.0 MPam.sup.1/2.
    Type: Grant
    Filed: April 17, 1985
    Date of Patent: April 7, 1987
    Assignee: Hercules Incorporated
    Inventors: Sung G. Chu, Harold Jabloner, Brian J. Swetlin
  • Patent number: 4645818
    Abstract: Heat-curable compositions are described, comprising(a) an epoxide resin and(b) an effective amount of a urea of formulaAr--NHCON(R.sup.3)R.sup.4whereAr represents an aromatic group linked through an aromatic carbon atom to the indicated nitrogen atom and which is substituted by an amido group, andR.sup.3 and R.sup.4 each represent an aliphatic, cycloaliphatic, or araliphatic hydrocarbyl group, optionally substituted by a halogen atom or a hydroxyl group, or R.sup.3 may further represent a hydrogen atom, or R.sup.3 nd R.sup.4, together with the indicated nitrogen atom, may represent a heterocyclic ring of 3 to 5 carbon atoms which may also have one oxygen atom in the ring.Such amidoarylureas may be used alone with the epoxide resin, or in combination with an accelerator for the heat-curing reaction, selected from dicyandiamide, carboxylic acid hydrazides, succinimide, cyanoacetamide, 1-cyano-3-(lower alkyl)guanidines, imidazoles, and carboxylic acid-tertiary amine salts.
    Type: Grant
    Filed: December 11, 1985
    Date of Patent: February 24, 1987
    Assignee: Ciba-Geigy Corporation
    Inventor: Christopher M. Andrews
  • Patent number: 4644036
    Abstract: Michael addition products of monocarboxylic or dicarboxylic acid esters, capable of undergoing Michael addition, with compounds containing double bonds capable of undergoing Michael addition are suitable for use as a curing component for synthetic resins containing groups capable of amide formation and/or ester formation with carboxylic acids. In particular, the Michael addition products of acetoacetic esters or malonic esters with esters, amides or urea derivatives of .alpha., .beta.-unsaturated monocarboxylic or dicarboxylic acids are used. The structure and the functionality of the curing component can be varied in many ways. It can be attached directly to the synthetic resin molecule, so that self-curing synthetic resins are obtained.
    Type: Grant
    Filed: April 26, 1984
    Date of Patent: February 17, 1987
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gerd Walz, Ernst-August Theiling
  • Patent number: 4621025
    Abstract: Disclosed is a composition of an epoxy resin and about 0.1 to about 2 moles per epoxy equivalent weight of a .beta.-diketo amide having the general formula ##STR1## where R.sub.1 is selected from the group consisting of alkyl to C.sub.20, aliphatic, cycloaliphatic, and arylalkyl, R.sub.2 is selected from the group consisting of hydrogen and R.sub.1, and R.sub.3 is selected from the group consisting of aryl and R.sub.1. A .beta.-diketo modified epoxy resin is also disclosed which has the general formula ##STR2## The .beta.-diketo modified epoxy resin is used in resin compositions to increase their adherence to metals and to chelate with metal containing catalysts, forming self-catalyzed resins.
    Type: Grant
    Filed: September 23, 1985
    Date of Patent: November 4, 1986
    Assignee: Westinghouse Electric Corp.
    Inventor: James D. B. Smith